Ethanol → 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

HRID 2091700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091700
Cl[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>COCCOC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8]

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 592500134-Chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

Produkt 1

HCID 592500334-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrileAusbeute 15,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile (0.200 g, 0.871 mmol), 2,4-dichlorophenylboronic acid (0.249 g, 1.31 mmol), bis(triphenylphosphine)palladium dichloride (0.061 g, 0.0871 mmol), sodium carbonate (0.184 g, 1.74 mmol) were taken up in DME (3 mL), ethanol (1 mL) and water (1 mL) and microwaved at 125° for 30 minutes. Mixture was diluted with ethyl acetate (10 mL) and extracted. The organic phase was dried with sodium sulfate, filtered and evaporated. ISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane afforded the title compound (45 mg, 15%). LCMS: (FA) ES+, 340. 1H NMR (400 MHz, d6-DMSO) δ: 7.44 (d, 1H), 7.20-7.17 (m, 2H), 3.43-3.28 (m, 4H), 3.16-2.93 (m, 4H).

Aufarbeitung

  1. extractionextracted
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-37e5806bf87046549cbf629a9c7fe705
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440664B2

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